


Betting on It

by Alyson



Series: 101 Ways to Fall [10]
Category: Star Trek: Alternate Original Series (Movies)
Genre: Academy Era, Crossdressing, Friends to Lovers, M/M, Silly
Language: English
Status: Completed
Published: 2019-05-27
Updated: 2019-05-27
Packaged: 2020-03-20 09:20:08
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,320
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18989788
Author URL: https://archiveofourown.org/users/Alyson/pseuds/Alyson
Summary: Jim lost a bet, but Bones feels like he's the one suffering the consequences.





	Betting on It

“Hey, Bones?”

“What's up, Jim?”

McCoy was working on a very important project, which was why he hadn't looked up when Kirk had keyed his way into his room or when he spoke. But he finally did when there was nothing else forthcoming from the other man. When he saw him, his jaw hit the ground.

“Yeah,” Jim pulled on the hem of his too short skirt. “I lost a bet.”

McCoy couldn't find the words. Jim was standing there, in his room, wearing what was traditionally known as the Academy's female uniform. There was a male skirt uniform, but it was cut for the male humanoid form. This wasn't. What Jim was wearing had clearly been cut for a woman and hadn't been adjusted for him, so it was too short and while it fit in the waist it clung to his thighs. It was hot. So McCoy decided to scowl at him.

“What the hell, Jim? Why didn't you go down and get uniforms that fit?”

“That's what you want to know?” Kirk asked, flabbergasted. “I only need them for a week, and besides, this was the deal. I have to wear the female uniform, not the male skirt uniform.”

“OK. So what was this bet you lost?”

“Ugh,” Jim walked over to McCoy's bed and collapsed on it face down, giving the doctor an unobstructed view of how well the skirt showed off his bottom. “I don't want to talk about it.”

Leonard didn't argue. He was too occupied with how far up the skirt had rucked, showing every inch of Jim's strong thighs, just barely keeping his ass covered. He tilted his head, shamelessly trying to see if he could see up the skirt. Jim wasn't wearing boxers and he was really curious as to what, exactly, he was wearing under there.

“Um, doesn't look like you could be wearing regulation boxers,” McCoy said as nonchalantly as possible. “Are you wearing anything?”

In response, Jim reached behind him and pulled the skirt up the rest of the way, exposing his round bottom, pale and bare, with just a T of red fabric at his tailbone.

“Are you wearing a thong!?” Bones choked.

“These things show panty lines like you wouldn't believe,” Jim responded, voice muffled by the pillow he still had his face shoved in.

If he had looked up he would have seen his best friend boggling at the sight of his legs and ass on full display and struggling to hide an erection. If he had looked up, his best friend would have seen the grin on his face.

*~*~*~*

As it turns out, Jim showing up to his room in a short uniform skirt was just him trying it on. It wasn't until the next day, the first full day of classes for the week, that the official week of the punishment Jim had somehow earned started. When McCoy walked across the quad that afternoon, heading towards the one class that he and Jim shared that semester and looking for the other man where he always waited for him so they could walk to class together, he got an eyeful. 

Jim was standing in the middle of a small group of admirers, one arm propped up on his friend Gary, leaning on him, his booted feet crossed at the ankles and the sun glinting off the gold in his hair. And not just the hair on his head. Leonard hadn't noticed in the lighting of his room the night before, but Jim hadn't bothered removing the hair on his legs. It made sense. He was only going to be in a skirt for a week and not all women removed their natural body hair, anyhow, but Leonard was still really glad to discover this. For some reason, those muscular, long, beautiful legs, glinting in the sunlight, was doing something for him.

“Hey, Jim, you ready to go?” he managed to get out, fighting a haze of lust from seeing what that skirt was doing for Jim's ass.

“Sure thing, Bones,” he replied with a bright smile, pulling away from his other friends. “Later, guys.”

It was then that McCoy realized Mitchell's arm had been around Jim's waist. He had been so preoccupied with Jim's butt and legs, he hadn't noticed at first. Once he did, though, jealousy shot through him so fiercely it took him by surprise. He stamped it down, knowing that that wasn't him. Jim may not return his own feelings, but he also knew with certainty he wasn't interested in Gary Mitchell, either. 

And did he really have to walk that way? McCoy was certain Jim was sauntering, putting those legs on display and swaying his hips. He shook his head and heaved a sigh, rolling his eyes at his friend.

“Alright, alright, I get it, you're wearing a dress,” McCoy said sarcastically once Jim got up beside him. “Stop your prancing and lets get to class.”

Kirk just laughed and walked normally beside him.

*~*~*~*

Class was a new sort of hell for McCoy. They sat mostly in the middle, on the fourth row of elevated seats, so everyone saw and stared before they caught themselves. Kirk, of course, didn't mind, just extended his legs out for the best view. The way he was slouching in his seat to put his legs on display also made his skirt hitch up just a little, something only McCoy could really see from where he was sitting right next to him. He took a moment to look his fill, seeing those lovely thighs in full and the glimpse of a hip. 

McCoy turned his eyes front, feeling his face heating up and his trousers becoming a bit too tight. Suddenly, he felt like a pervert, but he didn't exactly feel bad about it. No, he mostly just felt the desire to run his hand up the inside of Jim's thigh, find out what kind of fabric that thong was made of and how much of it actually covered him. He bet it covered a lot less if he was hard.

With some effort, he yanked his thoughts away from that path and watched as the professor took her position in front of the classroom and everyone settled down. Jim even sat up straight, prepping his PADD to take notes. Everything was fine for several minutes until the professor noticed Jim and stopped, her attention laser focused on him.

“Mr. Kirk,” she said, and waited for him to look up and acknowledge her. “While I applaud your attempt to bring back the fashion of male skirts, if you're going to wear one, you need to sit with the presence of mind that you're wearing one.”

Jim, and Leonard, were confused for all of a second, before Jim realized his was 'man-spreading' and closed his legs with an audible snap of his knees and a full blush to his face. Leonard blushed in sympathy and suddenly hoped for his friend's sake that thong was more appropriately made for a male - not the female one he had been fantasizing about - and nothing was hanging out.

*~*~*~*

The rest of the week went better for Jim as he adjusted to the awareness he needed while in a skirt. Leonard, however, was suffering just as badly as he had from day one. He had always kept his lust for his friend only in his fantasies, and his growing love for him close to his heart. He had never wanted to express either feeling for many good reasons. The lust, Jim could deal with. He was a good guy who didn't hold much against anyone and McCoy had never seen someone stay friends with former lovers the way Jim Kirk could. With very few exceptions, no one stayed mad long. But Leonard would never be satisfied with a one night stand or casual sex between friends, and he'd either end up scarring his friend away or destroying his own heart.

His own heart was another, probably more important, issue. It had been broken only a year before, the divorce finalized mere months ago. It was pieced back together in a fragile way and he was sure if it shattered again, it would simply disintegrate into dust and he'd never get it back together. He hated himself for his weakness, sometimes, but he was smart enough to realize he needed to make certain he could handle rejection and heart break before he put himself out there again.

Jim walking around with his legs all on display in a way that was strangely more tantalizing then when he walked around in just a towel or his gym shorts was making him forget why all that mattered.

It nearly came to a head Friday afternoon. Leonard had clinic hours and Jim had his hand to hand classes. Being a long time scrapper, he was talented at fighting and had a few tricks up his sleeves that his instructors were anxious for him to pass on to his fellow students, therefore he had been made a TA two years earlier than anyone else and spent the entire afternoon teaching the other students how to kick some serious ass. It didn't always go that well, though.

“Thank god, Bones,” McCoy heard Jim exclaim from the entrance to the clinic. He turned from where he had been leaning on the nurse's station, finishing up a patient file, and nearly blacked out.

Jim was walking towards him, blood dripping from the cloth he had pressed to his nose and more dripping down his leg. All the way down his leg. It started from somewhere in the back of his shorts. His incredibly, shorter than sin, tiny slit on the side, showing way more than they were hiding, shorts. He couldn't for the life of him figure out why he had been allowed to wear those in class, they barely covered the curve of his bottom. Then McCoy remembered the way Jim's instructor tended to ogle him while Jim was more covered and suddenly wanted to punch the man in the nose and give him a bleeder to match the one Jim was sporting.

“Jim, what the hell happened to you?” he finally asked once he got him into an exam room.

“Ugh, we were outside, running,” Jim explained as he gingerly climbed onto the exam table and lay face down. “I can't believe I did this. No one is going to let me live this down. I wasn't paying attention to where I was going, I was looking over my shoulder checking on the slower guys, and I ran right into a tree. I must have gone off the path just a little, you know how they like to plant those damn things right next to it. But I hit it so hard, I actually bounced. I went right down the embankment on the other side, slid down a brick wall on my left butt cheek. See?”

And then Jim was on hi knees, pulling the legs of his shorts up so high he was giving himself a wedgey, and tilting his ass up into the air. Thankfully, Dr. McCoy had taken over and he was preoccupied with the serious abrasion on that lovely butt cheek.

“Ow, Jim, that does look painful,” he grabbed a dermal regenerater and set to work. “Glad you got it cleaned up.”

“Yeah, wanted to see how bad it was before I bothered you with it.”

“You're not a bother, kid,” McCoy smiled. “If I don't have anything more serious, I'll patch up all your owies and boo-boos.”

Jim laughed and then gave a moan that could only be described as wanton.

“Damn, that's really feeling good.”

“Seriously? Are you getting aroused, right now?” he asked him with some disbelief.

“Sorry, Bones, can't help it,” Jim replied, not sounding nearly embarrassed enough. “You've got magic hands. Between that and the warmth and vibration of the regin, I'm about to burst out of these shorts.”

“Unbelievable,” he muttered, before he realized what Jim meant. His left hand had settled on Jim's bottom and was caressing a path between his cheek, around his hip and back again. He snatched his hand back as if he'd been burned.

“I'm sorry, Jim!”

“Hey, that's OK, Bones. I wasn't complaining.”

“Well, I'm ah, I'm done.”

Jim turned around and splayed himself out on the bed. Leonard was feeling guilty for feeling up his friend without permission, but not so much so that he didn't notice the long line of said friend's erection in the tiny shorts.

“You can't wear those short,” McCoy said more calmly than he felt. Way more. “They don't hide anything. You can't hide anything in those.”

“What's the big deal?” he shrugged. “You've seen me naked before. You've even seen me with an erection before, but that's because I forgot to lock the door. Boy, did you get an eyeful that day!”

“Yeah, I did,” McCoy groused, finally pulling his eyes away. “Let me check that nose of yours and maybe you can get that under control in the meantime.”

“Not if you're standing this close to me,” Jim responded with a leer.

McCoy helped him by resetting his nose – hard.

“Ow! Damn it, Bones! Fuck, that hurt!”

At least his shorts weren't as tight anymore.

*~*~*~*

The visit to the clinic made one thing abundantly clear to McCoy – Kirk would definitely fool around with him if he asked him. Clearly, his lust was returned, but that wasn't what McCoy wanted, and what he wanted wasn't what was on offer.

So he avoided him all of Friday. If he could get through the last day of the Jim Kirk skirt wearing fiasco, he'd be OK, and so far, Jim was cooperating with that plan. Bones got through all of his classes, his clinic hours and was able to finish up his project without seeing or hearing from the other cadet. He went to sleep that night feeling like he had accomplished more in one day than in the past four.

*~*~*~*

//”Bones! Sorry about yesterday, so much to do, so much attention. Drinks tonight?//

“Sure thing, Jim. Meet at my dorm?”

//”You got it! See you after your clinic duties! Wear something sexy!”//

Leonard disconnected the comm without responding to that last bit.

*~*~*~*

“I'm here, Bones!” McCoy heard from the bathroom where he was finishing up getting ready. “Hurry up, old man, I'm ready to dance and get my drink on!”

“Keep your pants on,” McCoy laughed as he came out of the bathroom, and stopped dead. “Where are your pants?”

Jim stood by his desk with a strip of fabric around his hips that couldn't actually be called a skirt. It was the shortest thing he had seen him in yet. McCoy was worried that there was no way the man's genitals could stay up in that, because he was right, he had seen him naked on a number of occasions, and there was no way he was fitting without some serious strapping up.

The shirt wasn't any better. A short sleeved cropped top that had BRAT emblazoned across it, it barely covered his pecs. If he lifted his arms, the doctor knew he'd be flashing the world at large his nipples. The look was completed with a pair of ankle boots, working with the not-skirt to show off as much of his incredible legs as possible. 

“Jim, the week is over.”

“Bones, a week is seven days. It was the whole week. I've still got today and tomorrow.”

“But, it was to wear the female uniform,” he tried to argue.

“Noooo, it was to wear female clothes. Had to borrow this little number from Gaila. The boots I bought, I have huge feet, but the whole look is rather flattering, don't you think?”

“I think,” McCoy snarled, closing the space between them and sliding his hands over the exposed waist of his best friend, “that you're trying to kill me.”

“Oh? What makes you think so?” Jim breathed as he took a step further into the doctor's personal space.

“Yeah, the shirt's right, you are a brat,” he grinned, sliding his hands down to finally cup Kirk's bottom. His fingers immediately found skin, the skirt doing nothing to cover him. He found the string of the thong and pulled it from between his cheeks. “You know damn well I'm attracted to you and you just had to tease me.”

“Not teasing, Bones,”Jim panted, grinding his newly erect cock against Leonard's hip. “You can have me. It's not teasing if it's for the taking.”

Jim lifted one leg up, hooking it over Leonard's hip, and kissed him roughly, tangling his fingers in his once neat hair. McCoy returned the kiss with equal passion, biting his lips, as he let his hands slide into the crevasse of Jim's ass, fingers brushing against his opening, finding it damp and pliable. He sunk two fingers in with ease, the molten passage already slick. Jim pulled back with a decadent moan and Leonard struggled to catch his breath.

“Looks like someone's already taken what was on offer,” he observed without any judgment. Jim smiled blearily at him.

“Oh, Bones, no one's taken me in months. I haven't been on offer since shortly after we got here,” he explained as he pumped his hips up and down on the fingers inside of him, grinding more firmly against the other man. “I just prepped myself. I thought for sure this piece of tshirt I cut out and slid on would do the trick. You really seem to like me in a skirt, or whatever you'd call this.”

“Guess it's the easy access,” he agreed and removed his hands long enough to steer Jim to his bed and lay him down on it. “And what do you mean you haven't been on offer? What have you been doing with Gaila all this time?”

“Mostly bitching about how you don't seem to want me even though it's clear you feel the same I do.”

McCoy had started shrugging out of his clothes while Jim spoke and was almost naked when Jim made a move to remove his own.

“Leave everything but the thong,” he growled. With a wicked glint in his eye, Jim did as told, shimmying out of a blue thong and tossing it aside. “You talking about just lust, kid?”

“Hell, no. I know you. I mean the whole package.”

Completely naked, Leonard crawled between the other man's splayed legs, Jim holding his thighs open wide for him, putting his entrance on display and lewdly running two of his fingers over the lax opening. Leonard gripped his cock and pressed the head against the fingers in his path, which Jim then pushed inside himself and used to spread his hole wide open. Bones pushed between them, sinking inside, until Jim was forced to remove his fingers and grip his thighs.

“Glad that's what you want,” Bones said in the roughest voice Jim had ever heard, then proceeded to give him the whole package, as requested.

*~*~*~*

“Was there really a bet?” McCoy asked much later.

“Yes, kinda,” Jim admitted. “It was actually a challenge. Gaila was tired of me complaining about our lack of romantic relationship, and me insisting it was important you make the first move, so she said you'd do it if I dressed sexy. I told her I did. She said, no, he's a leg man. Wear skirts. I said it wouldn't work. She bet me it would. So, I hadn't lost a bet. But I have now.”

“And what, pray tell, are you going to have to do now?” Leonard asked, almost afraid of the answer. Jim rolled over and propped himself up on Leonard's chest, giving him a mischievous smile.

“Gotta keep wearing the skirts for the rest of the month.”

“Bless that girl.”

The End

**Works inspired by this one:**

  * [Betting on it (Podfic version)](https://archiveofourown.org/works/20183131) by [kribban](https://archiveofourown.org/users/kribban/pseuds/kribban)




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